End-of-Year Newsletter: Setting You Up for a Smooth & Stress-Free Tax Season

Hello friends,

As we wrap up another year, I want to take a moment to say thank you for trusting me with your tax and financial needs. It’s truly a privilege to walk alongside you — through the challenges, the growth, the new opportunities, and everything in between.

Before we fully step into the holiday season, I want to offer a few hopeful reminders that will help make your upcoming tax filing experience as smooth and stress-free as possible. A little preparation now goes a long way toward clarity and confidence in the new year.

1. Take Time to Organize Your 2025 Tax Documents

January and February tend to bring a flood of tax forms. Set aside a dedicated folder — physical or digital — for items such as:

• W-2s and 1099s

• Brokerage statements

• Retirement contribution statements

• Mortgage interest and property tax documents

• Business income/expense summaries (if self-employed)

Even ten minutes of early organization can save you hours — and a headache — later.

2. Review Your Withholding or Estimated Tax Payments

If 2025 brought changes — a new job, a raise, business income shifts, rental property changes, or family updates — consider reviewing:

• Your W-4 withholding

• Your year-to-date estimated tax payments

Catching and correcting issues now prevents surprises come April.

3. Make Last-Minute Tax-Saving Moves (If Applicable)

There’s still time for smart year-end planning, such as:

• Contributing to a Traditional or Roth IRA

• Making last 2025 HSA contributions (if eligible)

• Donating to qualified charities

• Completing year-end business purchases or upgrades

• Paying certain deductible expenses before December 31

If you’re unsure what applies to you, feel free to ask — I’m here to guide you.

4. Gather Your Business or Rental Records Early

For my small business owners and rental property clients, now is an excellent moment to:

• Reconcile bookkeeping

• Compile receipts and mileage logs

• Review profit and loss reports

• Note major purchases or equipment acquisitions

• Confirm contractor W-9 forms are on file (for issuing 1099-NECs)

Clean books = a faster, easier tax filing. Remember, if you’re not using a bookkeeper for your small business, I will ask you to fill out my worksheet summary and sign it attesting to its accuracy and completeness.

Both worksheets are available as a free download on my website:

https://www.caslerfinancial.com/category/all-products

5. Make Space for Financial Reflection

This time of year is perfect for stepping back and asking:

• What worked financially in 2025?

• What felt stressful?

• What would I like to change in 2026?

• How can I simplify or strengthen my financial systems?

Clarity today creates confidence tomorrow.

6. Keep an Eye Out for Your Tax Organizer

In January, I’ll be sending out your annual Tax Organizer to help you gather everything I’ll need to prepare your return efficiently. This will come as an email from Casler Financial titled “Getting Ready For Tax Time” and will include our engagement letter, questionnaire, and space to upload your documents. Completing this thoroughly is one of the best ways to ensure accuracy and avoid delays. Although you will get this email in January, there is no rush to complete. As an existing client of ours, you do have until March 15th to get all your documents into us to ensure timely filing of your individual return by April 15th. (If you have an entity return such as a partnership or an S corporation, the deadline for those returns is March 15 so we would want to have all your data by February 15.)

Once the initial email goes out in mid January, you will get weekly reminders just to keep taxes on the forefront of your mind, but if you’re waiting on documents, you can just delete and ignore those emails until you’re ready to complete your organizer. Once you feel all the information needed to prepare your return is complete and uploaded, there will be a box for you to check that will alert alerts us to get started working on the return.

Closing Thoughts

I know taxes aren’t everyone’s favorite topic — but my goal is always to make the process as easy, clear, and encouraging as possible. You’re not alone in this. I’m here to help you move into the new year feeling grounded, organized, and supported.

Wishing you and your loved ones a joyful, peaceful holiday season and a hopeful start to 2026.

We also do have room for a handful of new individual clients so if you have any friends, family, or coworkers who are looking for a new tax preparer and you think they might be a good fit for our services, we would love an introduction 😊

Warmly,

Shay Bachelder

Casler Financial